Fluorine-containing bisphenols, their preparation, their precursors and intermediates, and use of the fluorine-containing bisphenols

Abstract

This invention relates to 1,2-di(4-hydroxyaryl)tetrafluoroethanes of the general formula (I) wherein R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoroalkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -polyfluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio, R 2 is C 1 -C 4 -alkyl, and n is an integer from 0 to 4. This invention further relates to the preparation of such compounds as well as to precursors and intermediates that can be used in their preparation.

1 . A process for preparing a compound of formula (V)  
       
         
           
           
               
               
           
         
       
       wherein 
 X is a halogen or pseudohalogen,  
 R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoroalkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -polyfluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio, and  
 n is an integer from 0 to 4,  
 comprising reacting a compound of formula (III)  
                     
 where  
 X is a halogen or pseudohalogen, 
 R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoro-alkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -poly-fluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio, and  
 n is an integer from 0 to 4,  
 with anhydrous hydrofluoric acid.  
 
 
     
     
         2 . A compound of formula (IV)  
       
         
           
           
               
               
           
         
       
       wherein 
 X is fluorine,  
 R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoroalkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -polyfluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio, and  
 n is an integer from 0 to 4.  
 
     
     
         3 . A method comprising preparing a polymer from diol monomers and hydroxy-reactive reactants wherein one or more of the monomers is a compound of formula I  
       
         
           
           
               
               
           
         
       
       wherein 
 R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoroalkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -polyfluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio,  
 R 2  is C 1 -C 4 -alkyl, and  
 n is an integer from 0 to 4.  
 
     
     
         4 . A method according to  claim 3  wherein the polymer is a polyester, a polyethers, or a polycarbonate.  
     
     
         5 . A method comprising preparing liquid crystals from one or more diol starting materials comprising compounds of formula (I)  
       
         
           
           
               
               
           
         
       
       wherein 
 R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoroalkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -polyfluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio,  
 R 2  is C 1 -C 4 -alkyl, and  
 n is an integer from 0 to 4.  
 
     
     
         6 . A method comprising preparing a flame retardant from one or more diol starting materials comprising compounds of formula (I)  
       
         
           
           
               
               
           
         
       
       wherein 
 R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -perfluoroalkyl, C 1 -C 4 -perfluoroalkoxy, C 1 -C 4 -perfluoroalkylthio, C 1 -C 4 -polyfluoroalkyl, C 1 -C 4 -polyfluoroalkoxy, or C 1 -C 4 -polyfluoroalkylthio,  
 R 2  is C 1 -C 4 -alkyl, and  
 n is an integer from 0 to 4.